Ammonium Chloride → 7-Octen-2-one

HRID 1879245Notes

Reaction equation

HRID 1879245 reaction equation
[CH3:1][Mg]Br.CON(C)[C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH3:1][C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 46703846N-methoxy-N-methylhept-6-enamideHCID 178418573HCID 178418573, compound

Product 1

HCID 193157-Octen-2-oneYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methyl magnesium bromide (3M in ether, 3 eq.) was added dropwise to a stirred mixture of N-methoxy-N-methylhept-6-enamide 58 in THF (0.1 M) cooled at 0° C. After sting for 1 h at 0° C., the mixture was poured into sat. aq. NH4Cl and diluted with EtOAc. The aqueous layer was further extracted with EtOAc, the combined organic layers were washed with brine and dried (Na2SO4). Evaporation of the solvent at 30 mbar afforded the title compound (96%) as a colorless oil. 1H NMR (400 MHz, CDCl3, 300 K) δ 5.81 (ddt, J 17.1, 10.3, 6.7, 1H), 5.02 (dd, J 17.1, 1.5, 1H), 4.97 (d, J 10.3, 1H), 2.46-2.43 (m, 2H), 2.15 (s, 3H), 2.10-2.05 (m, 2H), 1.65-1.57 (m, 2H), 1.45-1.37 (m, 2H).

Workup

  1. extractionThe aqueous layer was further extracted with EtOAc
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvent at 30 mbar

Sources & evidence

ORD record
ord-35db4e620f934f598ef1d1e024c64282
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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